We usually start with Clue and sometimes Monopoly (we want to play Illuminati, but haven't learned the rules) on Tabletop Simulator, then we switch to Drawful 2 and hopefully Quiplash (we need more players), to get the viewers involved.

Its kind of spur of the moment, but usually weekly, because my work schedule isn't fixed. I do give my discord, twitter, and steemit announcements a few hours before we play, usually in the evenings (anywhere between 6pm-9pm PST start, then go for 2-5 hours, depending on how many people show up for drawful).

Drawful 2 trailer:

Quiplash trailer:

Drawful (Pictionary w/ a twist) and Quiplash are hosted by me and only require a browser to play. The main screen is streamed on my twitch channel:

and players participate with (another open window) browser, phones, or tablets. We have a core group of three to five players. These games allow for up to eight, plus 10k more in audience participation.

This may be a better way to describe how to play Jackbox games:

If you're interested, you can follow me here or on twitter @bobloblaw45 (I don't check these too often, but I do post a few hours before we play and when I stream)
But the best way to contact me is through discord, I'm Bob Loblaw#0125. Ask for an invite to my discord channel! (let me know you're from steemit) And invite your friends! The more the merrier! It's always a hilarious time :D

We're a somewhat mature group. Not exactly kid friendly. We swear and joke and have a good time FYI.
Jeez this got long, quick. I need to make this a post :P